Aniline → Methyl 2-nitro-3-[(phenylimino)methyl]benzoate

HRID 655930Notes

Reaction equation

HRID 655930 reaction equation
[CH:1]([C:3]1[C:4]([N+:13]([O-:15])=[O:14])=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=O.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CCCCCC.CCOC(C)=O>CCO>[N+:13]([C:4]1[C:3]([CH:1]=[N:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 6115AnilineHCID 21226206Ethyl acetate hexaneHCID 44549250Methyl 3-formyl-2-nitrobenzoate

Product 1

HCID 44550023Methyl 2-nitro-3-[(phenylimino)methyl]benzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (A3) (1.0 eq.) and aniline (1.05 eq.) in EtOH (0.2 M) was stirred at reflux under N2 atmosphere for 2 hr until TLC revealed completation of the reaction (Hexane/EtOAc=75:25). Evaporation of the solvent gave (A4) as a white solid which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3, 300K) δ 8.51 (1H, d, J=7.3 Hz), 8.41 (1H, s), 8.11 (1H, d, J=7.8 Hz), 7.67 (1H, t, J=7.8 Hz), 7.43 (2H, t, J=7.8 Hz), 7.31 (1H, t, J=7.3 Hz), 7.16 (2H, d, J=7.8 Hz), 3.94 (3H, s).

Workup

  1. temperatureat reflux under N2 atmosphere for 2 hr until TLC
  2. customEvaporation of the solvent

Sources & evidence

ORD record
ord-ed2eb957d3bc449bbf363f462890a358
Source dataset
uspto-grants-2011_12
Patent number
US08071623B2

Reaction notes

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